Dodecandien-1-ol and dodecen-1-ol or mixtures thereof as aroma chemicals

ABSTRACT

The present invention relates to dodecandien-1-ol, dodecen-1-ol or mixtures thereof and a method of preparing same, to the use of dodecandien-1-ol, dodecen-1-ol or mixtures thereof as aroma chemical; to the use of dodecandien-1-ol, dodecen-1-ol or mixtures thereof for preparing an aroma chemical composition or for modifying the aroma character of an aroma chemical composition; to an aroma chemical composition containing dodecandien-1-ol, dodecen-1-ol or mixtures thereof; and to a method of preparing an aromatized composition or for modifying the aroma character of an aromatized composition.

The present invention relates to dodecandien-1-ol and dodecen-1-ol ormixtures thereof and a method of preparing the same, to the use ofdodecandien-1-ol and dodecen-1-ol or mixtures thereof as aroma chemical;to the use of dodecandien-1-ol and dodecen-1-ol or mixtures thereof forpreparing an aroma chemical composition or for modifying the aromacharacter of an aroma chemical composition; to an aroma chemicalcomposition containing dodecandien-1-ol and dodecen-1-ol or mixturesthereof; and to a method of preparing an aromatized composition or formodifying the aroma character of an aromatized composition.

TECHNICAL BACKGROUND

Aroma chemicals, especially fragrances, are of great interest,especially in the field of cosmetics and cleaning and laundrycompositions. Fragrances of natural origin are mostly expensive, oftenlimited in their available amount and, on account of fluctuations inenvironmental conditions, are also subject to variations in theircontent, purity etc. To circumvent these undesirable factors, it istherefore of great interest to create synthetic substances which haveorganoleptic properties that resemble more expensive natural fragrances,or which have novel and interesting organoleptic profiles.

Despite a large number of already existing synthetic aroma chemicals(fragrances and flavorings), there is a constant need for new componentsin order to be able to satisfy the multitude of properties desired forextremely diverse areas of application. These include, firstly, theorganoleptic properties, i.e. the compounds should have advantageousodiferous (olfactory) or gustatory properties. Furthermore, aromachemicals should also have additional positive secondary properties,such as e.g. an efficient preparation method, the possibility ofproviding better sensory profiles as a result of synergistic effectswith other fragrances, a higher stability under certain applicationconditions, a higher extendibility, a better higher substantivity, etc.

There is an increased need for aroma chemicals which can impart an aromaimpression, especially a woody/fruity/sweet/driedfruit/floral/orris/powdery/foodlike, odiferous impression to acomposition. Such properties are of special interest for compositionssuch as for example body care compositions, hygiene articles, cleaningcompositions, textile detergent compositions and compositions for scentdispensers. Of special interest are aroma chemicals, which can impartone or more distinct aroma impressions to a composition, therebycontributing to a rich and interesting sensory profile, especially anolfactory profile of the composition. In addition, especially regardingaroma chemicals which can impart an aroma impression, the substantivityas well as the tenacity are of special interest in order to obtain along-lasting odiferous impression in the composition as well as to thesurface with which the composition is treated.

However, since even small changes in chemical structure bring aboutmassive changes in the sensory properties such as odor and also taste,the targeted search for substances with certain sensory properties suchas a certain odor is extremely difficult. The search for new fragrancesand flavorings is therefore in most cases difficult and laboriouswithout knowing whether a substance with the desired odor and/or tastewill even actually be found.

It is an object of the presently claimed invention to provide new aromachemicals. These should have pleasant organoleptic properties.

It is a further object of the presently claimed invention to providesubstances which can be used as an aroma chemical in ready-to-usecompositions, in particular odor-intensive substances having a pleasantodor are sought. Furthermore, they should be combinable with other aromachemicals, allowing the creation of novel advantageous sensory profiles.In addition, these aroma chemicals should be obtainable from readilyavailable starting materials, allowing their fast and economicmanufacturing.

This object is achieved by the provision of the novel compoundsdodecandien-1-ol or dodecen-1-ol or mixtures thereof. The inventorsfound that these compound and/or mixtures have a pleasant odor which isreminiscent of an impression selected from the group consisting of analdehydic note, a fatty note, a mandarin note, a clean linen note, afloral note, a marine note, a citrus note, a metallic note, a waxy noteand a green note.

SUMMARY OF THE INVENTION

Thus, a first aspect of the presently claimed invention relates to theuse of compounds which are selected from the group consisting ofdodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol,4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol toimpart an aroma impression to a composition.

Specifically, the use of compounds selected from the group consisting ofdodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, toimpart an aroma impression to a composition.

A second aspect of the presently claimed invention relates to a methodof imparting an aroma impression to a composition comprising at leastthe step of adding a compound selected from the group consisting ofdodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol,4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol to acomposition.

Specifically, a method of imparting an aroma impression to a compositioncomprising at least the step of adding a compound selected from thegroup consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol,dodeca-4,11-dien-1-ol, to a composition.

A third aspect of the presently claimed invention relates to a mixturecomprising

-   a) at least one compound selected from the group consisting of    dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol and    dodeca-4,11-dien-1-ol; and-   b) at least one compound selected from the group consisting of    4-dodecen-1-ol, 8-dodecen-1-ol and 11-dodecen-1-ol; and-   c) dodecan-1-ol.

A fourth aspect of the presently claimed invention relates to an aromachemical composition comprising the compounds/the mixture of thepresently claimed invention and (i) at least one additional aromachemical different from the compounds of the presently claimedinvention, or (ii) at least one non-aroma chemical carrier, or (iii) amixture of (i) and (ii).

A fifth aspect of the presently claimed invention relates to the use ofa compound/a mixture of the presently claimed invention for preparing anaroma chemical composition.

A sixth aspect of the presently claimed invention relates to the use ofa compound/a mixture of the presently claimed invention for modifyingthe aroma character of an aroma chemical composition.

A seventh aspect of the presently claimed invention relates to a methodof preparing the compounds of the presently claimed invention.

A eighth aspect of the presently claimed invention relates to a methodof preparing an aroma chemical composition. Said method comprises thestep of mixing the compound of the presently claimed invention withother ingredients such as, e.g., at least one other aroma chemicaland/or at least one non-aroma chemical carrier to obtain the aromachemical composition.

A ninth aspect of the presently claimed invention relates to a method ofmodifying the aroma of an aroma chemical composition. Said methodcomprises the step of incorporating the compound of the presentlyclaimed invention into an aroma chemical composition to obtain anaroma-modified aroma chemical composition.

A tenth aspect of the presently claimed invention relates to a method ofmodifying the aroma of a ready-to-use composition. Said method comprisesthe step of incorporating the compound of the presently claimedinvention into a ready-to-use composition to obtain an aroma-modifiedready-to-use composition.

The compounds of the presently claimed invention and aroma chemicalcompositions thereof possess advantageous organoleptic properties, inparticular a pleasant aroma. Therefore, they can be favorably used asaromatizing ingredients in perfume compositions, body care compositions(including cosmetic compositions and products for oral and dentalhygiene), hygiene articles, cleaning compositions (including dishwashingcompositions), textile detergent compositions, compositions for scentdispensers, foods, food supplements, pharmaceutical compositions, cropprotection compositions and other ready-to-use compositions.

The pleasant aroma, low volatility and excellent solubility make thecompounds of the presently claimed invention a suitable ingredient incompositions where a pleasing aroma is desirable. By virtue of itsphysical properties, the compounds of the presently claimed inventionare well combinable with other aroma chemicals and customary ingredientsin aromatized ready-to-use compositions such as, in particular, perfumecompositions. This allows, e.g., the creation of aroma compositions, inparticular perfume compositions having novel advantageous sensoryprofiles.

Furthermore, the compounds of the presently claimed invention can beproduced in good yields and purities by a simple synthesis starting fromreadily available starting materials. Thus, the compounds of thepresently claimed invention can be produced in large scales and in asimple and cost-efficient manner.

DETAILED DESCRIPTION OF THE INVENTION

The following detailed description is merely exemplary in nature and isnot intended to limit the presently claimed invention or the applicationand uses of the presently claimed invention. Furthermore, there is nointention to be bound by any theory presented in the preceding technicalfield, background, summary or the following detailed description.

The terms “comprising”, “comprises” and “comprised of” as used hereinare synonymous with “including”, “includes” or “containing”, “contains”,and are inclusive or open-ended and do not exclude additional,non-recited members, elements or method steps. It will be appreciatedthat the terms “comprising”, “comprises” and “comprised of” as usedherein comprise the terms “consisting of”, “consists” and “consists of”.

Furthermore, the terms “(a)”, “(b)”, “(c)”, “(d)” etc. and the like inthe description and in the claims, are used for distinguishing betweensimilar elements and not necessarily for describing a sequential orchronological order. It is to be understood that the terms so used areinterchangeable under appropriate circumstances and that the embodimentsof the subject matter described herein are capable of operation in othersequences than described or illustrated herein. In case the terms “(A)”,“(B)” and “(C)” or AA), BB) and CC) or “(a)”, “(b)”, “(c)”, “(d)”,“(i)”, “(ii)” etc. relate to steps of a method or use or assay there isno time or time interval coherence between the steps, that is, the stepsmay be carried out simultaneously or there may be time intervals ofseconds, minutes, hours, days, weeks, months or even years between suchsteps, unless otherwise indicated in the application as set forth hereinabove or below.

In the following passages, different aspects of the subject matter aredefined in more detail. Each aspect so defined may be combined with anyother aspect or aspects unless clearly indicated to the contrary. Inparticular, any feature indicated as being preferred or advantageous maybe combined with any other feature or features indicated as beingpreferred or advantageous.

Reference throughout this specification to “one embodiment” or “anembodiment” or “preferred embodiment” means that a particular feature,structure or characteristic described in connection with the embodimentis included in at least one embodiment of the presently claimedinvention. Thus, appearances of the phrases “in one embodiment” or “In apreferred embodiment” or “in a preferred embodiment” in various placesthroughout this specification are not necessarily all referring to thesame embodiment but may refer. Furthermore, the features, structures orcharacteristics may be combined in any suitable manner, as would beapparent to a person skilled in the art from this disclosure, in one ormore embodiments. Furthermore, while some embodiments described hereininclude some, but not other features included in other embodiments,combinations of features of different embodiments are meant to be withinthe scope of the subject matter, and form different embodiments, aswould be understood by those in the art. For example, in the appendedclaims, any of the claimed embodiments are used in any combination.

Furthermore, the ranges defined throughout the specification include theend values as well, i.e. a range of 1 to 10 implies that both 1 and 10are included in the range. For the avoidance of doubt, the applicantshall be entitled to any equivalents according to applicable law.

Definitions

In the context of the present invention, the term “aroma” refers to asensory property and comprises an odor and/or a flavor.

The term “aroma chemical” denotes a substance which is used to obtain asensory or organoleptic (used interchangeably herein) impression andcomprises its use to obtain an olfactory and/or a flavor impression. Theterm “olfactory impression” denotes an odor impression without anypositive or negative judgement, while the term “scent impression” or“fragrance impression” or “aroma impression” (used interchangeablyherein) as used herein is connected to an odor impression which isgenerally felt as pleasant. Thus a “fragrance” or “scent” denotes anaroma chemical, which predominately induces a pleasant odor impression.A flavor induces a taste impression.

The term “aroma composition”, as used herein, refers to a compositionwhich induces an aroma. The term aroma composition comprises “odorcomposition” and/or “flavor composition”. An odor composition being acomposition, which predominately induces an odor impression, a flavorcomposition being a composition, which predominantly induces a tasteimpression.

The term odor composition comprises “fragrance composition” or “scentcomposition” (used interchangeably herein), which predominately inducean odor impression which is generally felt as pleasant.

The general hedonistic expressions “advantageous sensory properties” or“advantageous organoleptic properties” describe the niceness andconciseness of an organoleptic impression conveyed by an aroma chemical.“Niceness” and “conciseness” are terms which are familiar to the personskilled in the art, such as a perfumer. Niceness generally refers to aspontaneously brought about, positively perceived, pleasant sensoryimpression. However, “nice” does not have to be synonymous with “sweet”.“Nice” can also be the odor of musk or sandalwood. “Conciseness”generally refers to a spontaneously brought about sensory impressionwhich—for the same test panel—brings about a reproducibly identicalreminder of something specific. For example, a substance can have anodor which is spontaneously reminiscent of that of an “apple”: the odorwould then be concisely of “apples”. If this apple odor were verypleasant because the odor is reminiscent, for example, of a sweet, fullyripe apple, the odor would be termed “nice”. However, the odor of atypically tart apple can also be concise. If both reactions arise uponsmelling the substance, in the example thus a nice and concise appleodor, then this substance has particularly advantageous sensoryproperties.

The expressions “combination of”, “in combination with” or “combinedwith” when used herein referring to the compositions, methods or the useof two compounds, take account of the fact that the two compounds do notneed to be used in the form of a physical mixture of said compounds butcan be used (e.g., added) separately. Where the compounds are usedseparately, they can be used (e.g. added) sequentially (i.e. one afterthe other) in any order, or concurrently (i.e. basically at the sametime).

The term “boosting”, or “boost” is used herein to describe the effect ofenhancing and/or modifying the aroma of an aroma chemical or of acomposition. The term “enhancing” comprises an improvement of theniceness and/or conciseness of an aroma and/or an improvement of theintensity. The term “modifying” comprises the change of an aromaprofile.

The intensity can be determined via a threshold value determination. Athreshold value of an odor is the concentration of a substance in therelevant gas space at which an odor impression can just still beperceived by a representative test panel, although it no longer has tobe defined.

Booster effects are particularly desired in fragrance composition whentop-note-characterized applications are required, in which the odor isto be conveyed particularly quickly and intensively, for example indeodorants, air fresheners or in the taste sector in chewing gums.

The terms “the invention relates to” and “the invention is directed to”are used synonymously throughout the invention.

The terms “compound” and “substance” are used synonymously throughoutthe invention.

The term “tenacity” describes the evaporation behavior over time of anaroma chemical. The tenacity can for example be determined by applyingthe aroma chemical to a test strip, and by subsequent olfactoryevaluation of the odor impression of the test strip. For aroma chemicalswith high tenacity the time span after which the panel can stillidentify an aroma impression is long.

The term “substantivity” describes the interaction of an aroma chemicalwith a surface, such as for example the skin or a textile, especiallyafter subsequent treatment of the surface, such as for example washing.The substantivity can for example be determined by washing a textilewith a textile detergent composition comprising the aroma chemical andsubsequent olfactory evaluation of the textile directly after washing(wet textile) as well as evaluation of the dry textile after prolongedstorage.

The term “stability” describes the behavior of an aroma chemical uponcontact with oxygen, light and/or other substances. An aroma chemicalwith high stability maintains its aroma profile over a long period intime, preferably in a large variety of compositions and under variousstorage conditions.

In order to impart a long-lasting aroma impression to a composition orto a surface treated with a composition, the tenacity, the substantivityas well as the stability of the aroma chemical in the compositionsshould preferably be high.

Unless specified otherwise herein, a “compound” described herein anddesignations of compounds which are not stereospecific, such as “4,8dodecadien-1-ol” is not limited to any particular stereoisomer orparticular mixture of stereoisomers. Thus, the compound of the presentlyclaimed invention can be a single stereoisomer of 4,8 dodecadien-1-olselected from (4Z,8E)-dodeca-4,8-dien-1-ol,(4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol,(4Z,8Z)-dodeca-4,8-dien-1-ol or can be a mixture of two or more of thesestereoisomers of 4,8 dodecadien-1-ol.

Compound:

One embodiment of the presently claimed invention is directed to thecompounds selected from the group consisting of dodeca-4,8-dien-1-ol,dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol,8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol.

In a preferred embodiment, the compounds are selected from the groupconsisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol,dodeca-4,11-dien-1-ol.

In another embodiment of the presently claimed invention, the compoundof the presently claimed invention can be a single stereoisomer selectedfrom the group consisiting of (4Z,8E)-dodeca-4,8-dien-1-ol,(4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol,(4Z,8Z)-dodeca-4,8-dien-1-ol, (8E)-dodeca-4,8-dien-1-ol,(8Z)-dodeca-4,8-dien-1-ol, (4E)dodeca-4,11-dien-1-ol,(4Z)dodeca-4,11-dien-1-ol, (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol,(8E)-dodecen-1-ol, (8Z)-dodecen-1-ol and dodecan-1-ol.

Preferably, the compound of the presently claimed invention can be asingle stereoisomer selected from the group consisiting of4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol,(4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol,(8E)-dodeca-4,8-dien-1-ol, (8Z)-dodeca-4,8-dien-1-ol,(4E)dodeca-4,11-dien-1-ol, (4Z)dodeca-4,11-dien-1-ol.

Mixture

In yet another embodiment, the presently claimed invention is directedto a mixture comprising:

-   -   a) at least one compound selected from the group consisting of        dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol and        dodeca-4,11-dien-1-ol; and    -   b) at least one compound selected from the group consisting of        4-dodecen-1-ol, 8-dodecen-1-ol and 11-dodecen-1-ol.

In yet another embodiment of the presently claimed invention,dodeca-4,8-dien-1-ol is selected from the group consisting of(4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol,(4E,8E)-dodeca-4,8-dien-1-ol and (4Z,8Z)-dodeca-4,8-dien-1-ol.

In yet other embodiment of the presently claimed invention,dodeca-8,11-dien-1-ol is selected from the group consisting of(8E)-dodeca-4,8-dien-1-ol and (8Z)-dodeca-4,8-dien-1-ol.

In yet another embodiment of the presently claimed invention,dodeca-4,11-dien-1-ol is selected from the group consisting of (4E)dodeca-4,11-dien-1-ol and (4Z) dodeca-4,11-dien-1-ol.

In yet another embodiment of the presently claimed invention,4-dodecen-1-ol is selected from the group consisting of(4E)-dodecen-1-ol and (4Z)-dodecen-1-ol.

In a further embodiment of the presently claimed invention,8-dodecen-1-ol is selected from the group consisting of(8E)-dodecen-1-ol and (8Z)-dodecen-1-ol.

In an embodiment of the presently claimed invention, the mixture furthercomprises dodecan-1-ol.

Use:

One embodiment of the presently claimed invention is directed to the useof compounds selected from the group consisting of dodeca-4,8-dien-1-ol,dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol,8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol to impart an aromaimpression to a composition.

Preferably, the presently claimed invention is directed to the use ofcompounds selected from the group consisting of dodeca-4,8-dien-1-ol,dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol to impart an aromaimpression to a composition

In an embodiment of the presently claimed invention, the compoundsselected from the group consisting of (4Z,8E)-dodeca-4,8-dien-1-ol,(4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol,(4Z,8Z)-dodeca-4,8-dien-1-ol, (8E)-dodeca-4,8-dien-1-ol,(8Z)-dodeca-4,8-dien-1-ol, (4E)dodeca-4,11-dien-1-ol,(4Z)dodeca-4,11-dien-1-ol, (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol,(8E)-dodecen-1-ol, (8Z)-dodecen-1-ol and dodecan-1-ol are useful as anaroma chemical.

Preferably, the compounds selected from the group consisting of(4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol,(4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol,(8E)-dodeca-4,8-dien-1-ol, (8Z)-dodeca-4,8-dien-1-ol,(4E)dodeca-4,11-dien-1-ol, (4Z)dodeca-4,11-dien-1-ol, are useful as anaroma chemical

In an embodiment of the presently claimed invention, the compound/themixtures of the presently claimed invention or an aroma chemicalcomposition comprising said compounds/mixtures is used as a fragrance.

In particular, the compound of the presently claimed invention is usedto impart a note that is reminiscent of an aldehydic note, a fatty note,a mandarin note, a clean linen note, a floral note, a marine note, acitrus note, a metallic note, a waxy note, a violet leaf and a greennote.

The compound/mixture of the presently claimed invention can generally beused in a ready-to-use composition, in particular in an aromatizedready-to-use composition. “Aromatized ready-to-use composition”, as usedherein, refers to a ready-to-use composition which predominately inducesa pleasant odor and/or taste impression. In preferred embodiments, thearomatized ready-to-use composition is a scented ready-to-usecomposition, i.e. induces a pleasant odor.

Scented ready-to-use compositions are for example compositions used inpersonal care, in home care, in industrial applications as well ascompositions used in other applications, such as pharmaceuticalcompositions or crop protection compositions.

Preferably, the compound of the presently claimed invention is used in acomposition selected from the group consisting of perfume compositions,body care compositions (including cosmetic compositions and products fororal and dental hygiene), hygiene articles, cleaning compositions(including dishwashing compositions), textile detergent compositions,compositions for scent dispensers, foods, food supplements,pharmaceutical compositions and crop protection compositions. Thecompound of the presently claimed invention is used as an aromachemical, preferably as a fragrance, in the above compositions.

In particular, the compound of the presently claimed invention is usedto impart a note that is reminiscent of dried fruits, florals, sweets,orris, powdery elements; or is used to produce a scent that isreminiscent of sweets, florals, fruity elements to the above listedcompositions.

Details to the above-listed compositions are given below.

Similarly, the compound of the presently claimed invention can improvethe sensory profiles of aroma chemical compositions as a result ofsynergistic effects with other aroma chemical (e.g., other fragrances)comprised in the compositions, which means that the compound can providea booster effect for said other aroma chemicals. The compound istherefore suitable as a booster for other aroma chemicals.

Accordingly, the presently claimed invention also relates to the use ofthe compound of the presently claimed invention for modifying the aromacharacter (e.g., the scent character) of an aromatized (e.g.,fragranced) composition; and specifically, to the use as a booster forother aroma chemicals.

Booster effect of a substance means that the substance enhances andintensifies in aroma chemical formulations (such as, e.g., perfumeryformulations) the overall sensory (e.g., olfactory) impression of theformulation. In the mint range, for example, it is known that menthylmethyl ether intensifies the perfumery or taste mixtures of peppermintoils and particularly in top notes brings about a considerably moreintensive and more complex perception although the ether itself, being apure substance, develops no particular intensive odor at all. Infragrance applications, Hedione® (methyl dihydrojasmonate), which as apure substance only exhibits a light floral jasmine note, reinforcesdiffusion, freshness and volume of a perfume composition as an odorbooster. Booster effects are particularly desired whentop-note-characterized applications are required, in which the odorimpression is to be conveyed particularly quickly and intensively, forexample in deodorants, air fresheners or in the taste sector in chewinggums.

To achieve such a booster effect, the compound of the presently claimedinvention can be used, for example, in an amount of 0.001 to 10 wt. %(weight-%), such as in an amount of 0.01 to 2 wt. %, preferably from0.05 to 1 wt. %, in particular in an amount of from 0.1 to 0.5 wt. %,based on the total weight of the resulting aroma chemical composition.

Furthermore, the compound of the invention can have further positiveeffects on the composition in which it is used. For example, thecompound can enhance the overall performance of the composition intowhich it is incorporated, such as the stability, e.g. the formulationstability, the extendibility or the staying power of the composition.

Process:

Dodecandien-1-ol and dodecen-1-ol or mixtures thereof can be prepared bystandard methods of organic chemistry and by methods as described in theart. To be more precise, Dodecandien-1-ol and dodecen-1-ol or mixturesthereof can be prepared by subjecting 4,8,11-dodectrienal tohydrogenation to form Dodecandien-1-ol and dodecen-1-ol or mixturesthereof. Specifically, 4,8-Dodecadien-1-ol as well as 4-Dodecadien-1-oland 8-Dodecadien-1-ol as mixture of cis/trans isomers we obtained.

The reaction can be performed, e.g., in analogy to the method describedby Liebigs Annalen der Chemie (1982), (8), 1478-94.

In an embodiment, depending on hydrogenation time different ratio of thecorresponding alcohols can be obtained as determined by H-NMR (olefin vsmethylene).

In an embodiment, the catalysts used for the reaction is selected fromthe group consisting of ruthenium, iridium, rhodium, platinum,palladium.

In an embodiment the reaction was performed at a temperature in therange of 50° C. to 70° C., preferably 50° C. to 65° C., more preferably50° C. to 60° C.

In an embodiment, the reaction is carried out at pressure in the rangeof 25 bar to 40 bar, preferably 25 bar to 35 bar, more preferably 25 barto 30 bar.

In an embodiment, the reaction is carried out for 5 hours, 6 hours, 7hours, 8 hours, 9 hours, 10 hours, 11 hours, 12 hours, 13 hours, 14hours, 15 hours, ′6 hours, ′7 hours, 18 hours, 19 hours, 20 hours.

In an embodiment of the present invention, a tertiary amine is used as acatalyst/activator in the reaction. Preference is given totri-n-alkylamines, especially triethylamine, tri-n-propylamine,tri-n-butylamine and trimethylamine.

In an embodiment the 4,8,11-Dodecatrienal (1,2 Kg, 82 mmol) wasdissolved in methanol (800 g) in 3,5 L autoclave in the presence oftrimethylamine (48 g, 3 wt. %) and Ru/Fe-based catalyst (20 g, 1.6 wt.%). The hydrogenation reaction was performed at T=55° C. and 30 bar ofhydrogen pressure yielding 4,8-Dodecadien-1-ol as well as4-Dodecadien-1-ol and 8-Dodecadien-1-ol as mixture of cis/trans isomers

In an embodiment, the reaction time was 6 hours and the percentage ofdodecenol and dodecadienol obtained was 12% and 88% respectively.

In yet another embodiment, the reaction time was 8 hours and thepercentage of dodecenol and dodecadienol obtained was 40% and 60%respectively.

In a further embodiment, the reaction time was 14 hours and thepercentage of dodecenol and dodecadienol obtained was 66% and 34%respectively.

Composition:

In an embodiment, the presently claimed invention relates to an aromachemical composition comprising the compounds/mixture of the inventionand:

(i) at least one additional aroma chemical, or

(ii) at least one non-aroma chemical carrier, or

(iii) both of (i) and (ii).

The term “aroma chemical composition”, as used herein, refers to acomposition which induces a pleasant aroma, e.g., a pleasant odorimpression.

The non-aroma chemical carrier in the aroma chemical composition of theinvention can be, in particular, selected from surfactants, oilcomponents and solvents.

The additional aroma chemical is different from the compound/mixture ofthe presently claimed invention.

By virtue of its physical properties, the compounds/mixtures are wellcombinable with other aroma chemicals (e.g., other fragrances) and othercustomary ingredients in aromatized (e.g., fragranced) ready to usecompositions such as, in particular, perfume compositions. This allows,e.g., the creation of aroma compositions (e.g., perfume compositions)which have novel advantageous sensory profiles. Especially, as alreadyexplained above, the compound can provide a booster effect for otheraroma chemicals (such as other fragrances).

Accordingly, in one preferred embodiment, the aroma chemical compositioncomprises a compound of the presently claimed invention, as definedherein; and at least one additional aroma chemical that is differentfrom the compound/mixture of the presently claimed invention.

The additional aroma chemical can for example be one, preferably 2, 3,4, 5, 6, 7, 8 or further aroma chemicals, selected from the groupconsisting of:

geranyl acetate, alpha-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate,dihydromyrcenol, methyl dihydrojasmonate,4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran,tetrahydrolinalool, ethyllinalool, benzyl salicylate,2-methyl-3-(4-tert-butylphenyl)propanal, cinnamyl alcohol,4,7-methano-3a,4,5,6,7,7a-hexahydro-5-indenyl acetate and/or4,7-methano-3a,4,5,6,7,7a-hexahydro-6-indenyl acetate, citronellol,citronellyl acetate, tetrahydrogeraniol, vanillin, linalyl acetate,styrolyl acetate, octahydro-2,3,8,8-tetramethyl-2-acetonaphthone and/or2-acetyl-1,2,3,4,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene, hexylsalicylate, 4-tert-butylcyclohexyl acetate, 2-tert-butylcyclohexylacetate, alpha-ionone, n-alpha-methylionone, alpha-isomethylionone,coumarin, terpinyl acetate, 2-phenylethyl alcohol,4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-carboxaldehyde,alpha-amylcinnamaldehyde, ethylene brassylate, (E)- and/or(Z)-3-methylcyclopentadec-5-enone, 15-pentadec-11-enolide and/or15-pentadec-12-enolide, 15-cyclopentadecanolide,1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)ethanone,2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol,2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol,cis-3-hexenyl acetate, trans-3-hexenyl acetate,trans-2/cis-6-nonadienol, 2,4-dimethyl-3-cyclohexenecarboxaldehyde,2,4,4,7-tetramethyloct-6-en-3-one, 2,6-dimethyl-5-hepten-1-al, borneol,3-(3-isopropylphenyl)butanal,2-methyl-3-(3,4-methylenedioxyphenyl)propanal,3-(4-ethylphenyl)-2,2-dimethylpropanal,7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 3,3,5-trimethylcyclohexylacetate, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol,3-(4-tert-butylphenyl)-propanal, ethyl 2-methylpentanoate,ethoxymethoxycyclododecane,2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine,(2-tert-butylcyclohexyl) acetate and3-[5,5,6-trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1-ol.

In yet another preferred embodiment, the at least one aroma chemical (i)is selected from the group consisting of methyl benzoate, benzylacetate, geranyl acetate, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol,linalool, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol and methylbenzoate.

In yet another preferred embodiment, the at least one aroma chemical (i)is selected from the group consisting of ethylvanillin, vanillin,2,5-dimethyl-4-hydroxy-2H-furan-3-one (furaneol) or3-hydroxy-2-methyl-4H-pyran-4-one (maltol).

Further aroma chemicals with which the compound of the present inventioncan be combined to give a composition according to the presently claimedinvention can be found, e.g., in S. Arctander, Perfume and FlavorChemicals, Vol. I and II, Montclair, N. J., 1969, self-published or K.Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials,4th Ed., Wiley-VCH, Weinheim 2001. Specifically, mention may be made of:

extracts from natural raw materials such as essential oils, concretes,absolutes, resins, resinoids, balsams, tinctures such as e.g.

ambergris tincture; amyris oil; angelica seed oil; angelica root oil;aniseed oil; valerian oil; basil oil; tree moss absolute; bay oil;mugwort oil; benzoin resin; bergamot oil; beeswax absolute; birch taroil; bitter almond oil; savory oil; buchu leaf oil; cabreuva oil; cadeoil; calmus oil; camphor oil; cananga oil; cardamom oil; cascarilla oil;cassia oil; cassia absolute; castoreum absolute; cedar leaf oil; cedarwood oil; cistus oil; citronella oil; lemon oil; copaiba balsam; copaibabalsam oil; coriander oil; costus root oil; cumin oil; cypress oil;davana oil; dill weed oil; dill seed oil; Eau de brouts absolute; oakmoss absolute; elemi oil; tarragon oil; eucalyptus citriodora oil;eucalyptus oil; fennel oil; pine needle oil; galbanum oil; galbanumresin; geranium oil; grapefruit oil; guaiacwood oil; gurjun balsam;gurjun balsam oil; helichrysum absolute; helichrysum oil; ginger oil;iris root absolute; iris root oil; jasmine absolute; calmus oil;camomile oil blue; roman camomile oil; carrot seed oil; cascarilla oil;pine needle oil; spearmint oil; caraway oil; labdanum oil; labdanumabsolute; labdanum resin; lavandin absolute; lavandin oil; lavenderabsolute; lavender oil; lemongrass oil; lovage oil; lime oil distilled;lime oil pressed; linalool oil; litsea cubeba oil; laurel leaf oil; maceoil; marjoram oil; mandarin oil; massoia bark oil; mimosa absolute; muskseed oil; musk tincture; clary sage oil; nutmeg oil; myrrh absolute;myrrh oil; myrtle oil; clove leaf oil; clove flower oil; neroli oil;olibanum absolute; olibanum oil; opopanax oil; orange blossom absolute;orange oil; origanum oil; palmarosa oil; patchouli oil; perilla oil;peru balsam oil; parsley leaf oil; parsley seed oil; petitgrain oil;peppermint oil; pepper oil; pimento oil; pine oil; pennyroyal oil; roseabsolute; rose wood oil; rose oil; rosemary oil; Dalmatian sage oil;Spanish sage oil; sandalwood oil; celery seed oil; spike-lavender oil;star anise oil; styrax oil; tagetes oil; fir needle oil; tea tree oil;turpentine oil; thyme oil; tolubalsam; tonka absolute; tuberoseabsolute; vanilla extract; violet leaf absolute; verbena oil; vetiveroil; juniper berry oil; wine lees oil; wormwood oil; winter green oil;hyssop oil; civet absolute; cinnamon leaf oil; cinnamon bark oil, andfractions thereof, or ingredients isolated therefrom; individualfragrances from the group of hydrocarbons, such as e.g. 3 carene;alpha-pinene; beta-pinene; alpha-terpinene; gamma-terpinene; p-cymene;bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene;longifolene; myrcene; ocimene; valencene; (E,Z)-1,3,5-undecatriene;styrene; diphenylmethane;

the aliphatic alcohols such as e.g. hexanol; octanol; 3-octanol;2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol;(E)-2-hexenol; (E)- and (Z)-3-hexenol; 1 octen-3-ol; mixture of3,4,5,6,6-pentamethyl-3/4-hepten-2-ol and3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; (E,Z)-2,6-nonadienol;3,7-dimethyl-7-methoxyoctan-2-ol; 9-decenol; 10-undecenol;4-methyl-3-decen-5-ol;

the aliphatic aldehydes and acetals thereof such as e.g. hexanal;heptanal; octanal; nonanal; decanal; undecanal; dodecanal; tridecanal;2-methyloctanal; 2-methylnonanal; (E)-2-hexenal; (Z)-4-heptenal;2,6-dimethyl-5-heptenal; 10-undecenal; (E)-4-decenal; 2-dodecenal;2,6,10-trimethyl-9-undecenal; 2,6,10 trimethyl-5,9-undecadienal;heptanal diethylacetal; 1,1-dimethoxy-2,2,5 trimethyl-4-hexene;citronellyloxyacetaldehyde; (E/Z)-1-(1-methoxypropoxy)-hex-3-ene; thealiphatic ketones and oximes thereof such as e.g. 2-heptanone;2-octanone; 3-octanone; 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3heptanone oxime; 2,4,4,7-tetramethyl-6-octen-3-one;6-methyl-5-hepten-2-one;

the aliphatic sulfur-containing compounds such as e.g.3-methylthiohexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol;3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexylacetate; 1-menthene-8-thiol;

the aliphatic nitriles such as e.g. 2-nonenenitrile; 2-undecenenitrile;2 tridecenenitrile; 3,12-tridecadienenitrile;3,7-dimethyl-2,6-octadienenitrile; 3,7-dimethyl-6 octenenitrile;

the esters of aliphatic carboxylic acids such as e.g. (E) and(Z)-3-hexenyl formate; ethyl acetoacetate; isoamyl acetate; hexylacetate; 3,5,5-trimethylhexyl acetate; 3 methyl-2-butenyl acetate;(E)-2-hexenyl acetate; (E) and (Z)-3-hexenyl acetate; octyl acetate;3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; butyl butyrate;isoamyl butyrate; hexyl butyrate; (E) and (Z)-3-hexenyl isobutyrate;hexyl crotonate; ethyl isovalerate; ethyl 2-methylpentanoate; ethylhexanoate; allyl hexanoate; ethyl heptanoate; allyl heptanoate; ethyloctanoate; ethyl (E,Z)-2,4-decadienoate; methyl 2-octinate; methyl2-noninate; allyl 2-isoamyloxy acetate;methyl-3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl crotonate;

the acyclic terpene alcohols such as e.g. geraniol; nerol; linalool;lavandulol; nerolidol; farnesol; tetrahydrolinalool;2,6-dimethyl-7-octen-2-ol; 2,6-dimethyloctan-2-ol;2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5,7-octadien-2-ol;2,6-dimethyl-3,5-octadien-2 ol; 3,7-dimethyl-4,6-octadien-3-ol;3,7-dimethyl-1,5,7-octatrien-3-ol; 2,6-dimethyl-2,5,7-octatrien-1-ol;and the formates, acetates, propionates, isobutyrates, butyrates,isovalerates, pentanoates, hexanoates, crotonates, tiglinates and3-methyl-2 butenoates thereof;

the acyclic terpene aldehydes and ketones such as e.g. geranial; neral;citronellal; 7 hydroxy-3,7-dimethyloctanal; 7methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9 undecenal; geranylacetone; as well as the dimethyl and diethylacetals of geranial, neral,7-hydroxy-3,7-dimethyloctanal; the cyclic terpene alcohols such as e.g.menthol; isopulegol; alpha-terpineol; terpine-4-ol; menthan-8-ol;menthan-1-ol; menthan-7-ol; borneol; isoborneol; linalool oxide; nopol;cedrol; ambrinol; vetiverol; guajol; and the formates, acetates,propionates, isobutyrates, butyrates, isovalerates, pentanoates,hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates thereof;

the cyclic terpene aldehydes and ketones such as e.g. menthone;isomenthone; 8 mercaptomenthan-3-one; carvone; camphor; fenchone;alpha-ionone; beta-ionone; alpha-n-methylionone; beta-n-methylionone;alpha-isomethylionone; beta-isomethylionone; alpha-irone;alpha-damascone; beta-damascone; beta-damascenone; delta-damascone;gamma-damascone; 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one;1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methano-,naphthalene-8(5H)-one;2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal; nootkatone;dihydronootkatone; 4,6,8-megastigmatrien-3-one; alpha-sinensal;beta-sinensal; acetylated cedar wood oil (methyl cedryl ketone);

the cyclic alcohols such as e.g. 4-tert-butylcyclohexanol;3,3,5-trimethylcyclohexanol; 3-isocamphylcyclohexanol;2,6,9-trimethyl-Z2,Z5,E9-cyclododecatrien-1-ol;2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;

the cycloaliphatic alcohols such as e.g.alpha-3,3-trimethylcyclohexylmethanol; 1 (4-isopropylcyclohexyl)ethanol;2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)butanol; 2-methyl-4-(2,2,3trimethyl-3-cyclopent-1-yl)-2-buten-1-ol; 2-ethyl-4-(2,2,3-trimethyl-3cyclopent-1-yl)-2-buten-1-ol; 3-methyl-5-(2,2,3trimethyl-3-cyclopent-1-yl)pentan-2 ol;3-methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol;3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol;1-(2,2,6-trimethylcyclohexyl)pentan-3-ol;1-(2,2,6-trimethylcyclohexyl)hexan-3-ol;

the cyclic and cycloaliphatic ethers such as e.g. cineol; cedryl methylether; cyclododecyl methyl ether; 1,1-dimethoxycyclododecane;(ethoxymethoxy)cyclo-dodecane; alpha-cedrene epoxide;3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan;3a-ethyl-6,6,9a-trimethyldodecahydro-naphtho[2,1-b]furan;1,5,9-trimethyl-13-oxabicyclo-[10.1.0]trideca-4,8-diene; rose oxide;2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxane;

the cyclic and macrocyclic ketones such as e.g.4-tert-butylcyclohexanone; 2,2,5 trimethyl-5-pentylcyclopentanone;2-heptylcyclopentanone; 2-pentylcyclopentanone;2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one;3-methyl-4-cyclopenta-decenone; 3-methyl-5-cyclopentadecenone;3-methylcyclopentadecanone;4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone;4-tert-pentylcyclohexanone; 5-cyclohexadecen-1-one;6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone;8-cyclo-hexadecen-1-one; 7-cyclohexadecen-1-one;(7/8)-cyclohexadecen-1-one; 9 cyclo-heptadecen-1-one;cyclopentadecanone; cyclohexadecanone;

the cycloaliphatic aldehydes such as e.g.2,4-dimethyl-3-cyclohexenecarbaldehyde; 2methyl-4-(2,2,6-trimethylcyclohexen-1-yl)-2-butenal;4-(4-hydroxy-4-methylpentyl)-3 cyclohexene carbaldehyde;4-(4-methyl-3-penten-1-yl)-3-cyclohexenecarbaldehyde;

the cycloaliphatic ketones such as e.g.1-(3,3-dimethylcyclohexyl)-4-penten-1-one; 2,2dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanone;1-(5,5-dimethyl-1 cyclo-hexen-1-yl)-4-penten-1-one;2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methylketone; methyl 2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone;tert-butyl (2,4-dimethyl-3-cyclohexen-1-yl) ketone;

the esters of cyclic alcohols such as e.g. 2-tert-butylcyclohexylacetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexylacetate; 4-tert-pentylcyclohexyl acetate; 3,3,5-trimethylcyclohexylacetate; decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentylcrotonate; 3-pentyltetrahydro-2H-pyran-4-yl acetate;decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate;4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl acetate;4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6 indenyl propionate;4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl isobutyrate; 4,7methanooctahydro-5 or 6-indenyl acetate;

the esters of cycloaliphatic alcohols such as e.g. 1-cyclohexylethylcrotonate;

the esters of cycloaliphatic carboxylic acids such as e.g. allyl3-cyclohexylpropionate; allyl cyclohexyloxyacetate; cis and trans-methyldihydrojasmonate; cis and trans-methyl jasmonate; methyl2-hexyl-3-oxocyclopentanecarboxylate; ethyl 2-ethyl-6,6dimethyl-2-cyclohexenecarboxylate; ethyl 2,3,6,6-tetramethyl-2cyclohexenecarboxylate; ethyl 2-methyl-1,3-dioxolane-2-acetate;

the araliphatic alcohols such as e.g. benzyl alcohol; 1-phenylethylalcohol, 2 phenylethyl alcohol, 3-phenylpropanol; 2-phenylpropanol;2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol;2,2-dimethyl-3-(3-methylphenyl)propanol; 1,1-dimethyl-2 phenylethylalcohol; 1,1-dimethyl-3-phenylpropanol;1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol;3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxy-benzylalcohol; 1-(4-isopropylphenyl)ethanol;

the esters of araliphatic alcohols and aliphatic carboxylic acids suchas e.g. benzyl acetate; benzyl propionate; benzyl isobutyrate; benzylisovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate;2-phenylethyl isobutyrate; 2 phenylethyl isovalerate; 1 phenylethylacetate; alpha-trichloromethylbenzyl acetate;alpha,alpha-dimethylphenylethyl acetate; alpha,alpha-dimethylphenylethylbutyrate; cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzylacetate;

the araliphatic ethers such as e.g. 2-phenylethyl methyl ether; 2phenylethyl isoamyl ether; 2-phenylethyl 1-ethoxyethyl ether;phenylacetaldehyde dimethyl acetal; phenylacetaldehyde diethyl acetal;hydratropaaldehyde dimethyl acetal; phenylacetaldehyde glycerol acetal;2,4,6-trimethyl-4-phenyl-1,3-dioxane;4,4a,5,9b-tetrahydroindeno[1,2-d]-m-dioxine;4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m dioxine;

the aromatic and araliphatic aldehydes such as e.g. benzaldehyde;phenylacetaldehyde; 3-phenylpropanal; hydratropaaldehyde;4-methylbenzaldehyde; 4 methylphenylacetaldehyde;3-(4-ethylphenyl)-2,2-dimethylpropanal;2-methyl-3-(4-isopropylphenyl)propanal;2-methyl-3-(4-tert-butylphenyl)propanal;2-methyl-3-(4-isobutylphenyl)propanal; 3-(4-tert-butylphenyl)propanal;cinnamaldehyde; alpha-butylcinnamaldehyde; alpha-amylcinnamaldehyde;alpha-hexylcinnamaldehyde; 3 methyl-5-phenylpentanal;4-methoxybenzaldehyde; 4-hydroxy-3 methoxy-benzaldehyde;4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde;3,4-dimethoxybenzaldehyde; 2-methyl-3-(4-methoxyphenyl)propanal;2-methyl-3-(4-methylenedioxyphenyl)propanal;

the aromatic and araliphatic ketones such as e.g. acetophenone;4-methylacetophenone; 4-methoxyacetophenone;4-tert-butyl-2,6-dimethylaceto-phenone; 4-phenyl-2-butanone;4-(4-hydroxyphenyl)-2-butanone; 1-(2-naphthalenyl)-ethanone;2-benzofuranylethanone; (3-methyl-2-benzofuranyl)ethanone;benzo-phenone; 1,1,2,3,3,6-hexamethyl-5-indanyl methyl ketone;6-tert-butyl-1,1 dimethyl-4 indanyl methyl ketone;1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5indenyl]ethanone;5′,6′,7′,8′-tetrahydro-3′,5′,5′,6′,8′,8′-hexamethyl-2-acetonaphthone;

the aromatic and aliphatic carboxylic acids and esters thereof such ase.g. benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate;hexyl benzoate; benzyl benzoate; methyl phenylacetate; ethylphenylacetate; geranyl phenylacetate; phenylethyl phenylacetate; methylcinnamate; ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate;cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; isoamylsalicylate; hexyl salicylate; cyclohexyl salicylate; cis-3-hexenylsalicylate; benzyl salicylate; phenylethyl salicylate; methyl2,4-dihydroxy-3,6-dimethylbenzoate; ethyl 3-phenylglycidate; ethyl3-methyl-3-phenylglycidate;

the nitrogen-containing aromatic compounds such as e.g.2,4,6-trinitro-1,3-dimethyl-tert-butylbenzene;3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone; cinnamonitrile; 3methyl-5-phenyl-2-pentenonitrile; 3-methyl-5-phenylpentanonitrile;methyl anthranilate; methyl-N-methylanthranilate; Schiff bases of methylanthranilate with 7 hydroxy-3,7-dimethyloctanal,2-methyl-3-(4-tert-butylphenyl)propanal or 2,4dimethyl-3-cyclohexenecarbaldehyde; 6-isopropylquinoline;6-isobutylquinoline; 6-sec-butylquinoline; 2-(3-phenylpropyl)pyridine;indole; skatole; 2-methoxy-3 isopropyl-pyrazine;2-isobutyl-3-methoxypyrazine;

the phenols, phenyl ethers and phenyl esters such as e.g. estragole;anethole; eugenol; eugenyl methyl ether; isoeugenol; isoeugenyl methylether; thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether;beta-naphthyl ethyl ether; beta-naphthyl isobutyl ether;1,4-dimethoxybenzene; eugenyl acetate; 2-methoxy-4-methylphenol; 2ethoxy-5-(1-propenyl)phenol; p-cresyl phenylacetate;

the heterocyclic compounds such as e.g.2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2ethyl-4-hydroxy-5-methyl-2H-furan-3-one;3-hydroxy-2-methyl-4H-pyran-4-one; 2 ethyl-3-hydroxy-4H-pyran-4-one;

the lactones such as e.g. 1,4-octanolide; 3-methyl-1,4-octanolide;1,4-nonanolide; 1,4-decanolide; 8-decen-1,4-olide; 1,4-undecanolide;1,4-dodecanolide; 1,5-decanolide; 1,5-dodecanolide;4-methyl-1,4-decanolide; 1,15-pentadecanolide; cis andtrans-11-pentadecen-1,15-olide; cis and trans-12-pentadecen-1,15-olide;1,16-hexadecanolide; 9-hexadecen-1,16-olide; 10-oxa-1,16-hexadecanolide;11-oxa-1,16-hexadecanolide; 12-oxa-1,16-hexadecanolide; ethylene1,12-dodecanedioate; ethylene 1,13-tridecanedioate; coumarin;2,3-dihydrocoumarin; octahydrocoumarin. In a preferred embodiment, theat least one non-aroma chemical carrier (ii) is selected from the groupconsisting of surfactants, oil components, anti-oxidants,deodorant-active agents and solvents.

In the context of the presently claimed invention, a “solvent” servesfor the dilution of the compound of the present invention to be usedaccording to the invention and/or any further component of thecomposition without having its own aroma.

The amount of solvent(s) is selected depending on the composition.

In yet another preferred embodiment, the solvent is selected from thegroup consisting of ethanol, isopropanol, diethylene glycol monoethylether, glycerol, propylene glycol, 1,2-butylene glycol, dipropyleneglycol, triethyl citrate and isopropyl myristate.

In yet another preferred embodiment, the solvent is present in thecomposition in an amount of 0.01 wt. % to 99.0 wt. %, more preferably inan amount of 0.05 wt. % to 95.0 wt. %, yet more preferably in an amountof 0.1 wt. % to 80.0 wt. %, most preferably 0.1 wt. % to 70.0 wt. %,particularly in an amount of 0.1 wt. % to 60.0 wt. %, based on the totalweight of the composition.

In yet another preferred embodiment of the invention, the compositioncomprises 0.05 wt. % to 10 wt. %, more preferably 0.1 wt. % to 5 wt. %,yet more preferably 0.2 wt. % to 3 wt. % solvent(s), based on the totalweight of the composition. In yet another preferred embodiment of theinvention, the composition comprises 20 wt. % to 70 wt. %, morepreferably 25 wt. % to 50 wt. % of solvent(s), based on the total weightof the composition.

One embodiment of the invention is directed to a composition comprisingthe compound of the present invention and at least one oil component.

In a preferred embodiment, the oil components are present in an amountof 0.1 to 80 wt. %, more preferably 0.5 to 70 wt. %, yet more preferably1 to 60 wt. %, even more preferably 1 to 50 wt. %, particularly 1 to 40wt. %, more particularly 5 to 25 wt. % and specifically 5 to 15 wt. %,based on the total weight of the composition.

The oil components may be selected, for example, from Guerbet alcoholsbased on fatty alcohols containing 6 to 18, preferably 8 to 10, carbonatoms and other additional esters, such as myristyl myristate, myristylpalmitate, myristyl stearate, myristyl isostearate, myristyl oleate,myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate,cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetylerucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearylisostearate, stearyl oleate, stearyl behenate, stearyl erucate,isostearyl myristate, isostearyl palmitate, isostearyl stearate,isostearyl isostearate, isostearyl oleate, isostearyl behenate,isostearyl oleate, oleyl myristate, oleyl palmitate, oleyl stearate,oleyl isostearate, oleyl oleate, oleyl behenate, oleyl erucate, behenylmyristate, behenyl palmitate, behenyl stearate, behenyl isostearate,behenyl oleate, behenyl behenate, behenyl erucate, erucyl myristate,erucyl palmitate, erucyl stearate, erucyl isostearate, erucyl oleate,erucyl behenate and erucyl erucate. Also suitable are esters of C18-C38alkyl-hydroxycarboxylic acids with linear or branched C6-C22 fattyalcohols, more especially dioctyl malate, esters of linear and/orbranched fatty acids with polyhydric alcohols (for example propyleneglycol, dimer dial or trimer triol), triglycerides based on C6-C10 fattyacids, liquid mono-, di- and triglyceride mixtures based on C6-C18 fattyacids, esters of C6-C22 fatty alcohols and/or Guerbet alcohols witharomatic carboxylic acids, more particularly benzoic acid, esters ofdicarboxylic acids with polyols containing 2 to 10 car-bon atoms and 2to 6 hydroxyl groups, vegetable oils, branched primary alcohols,substituted cyclohexanes, linear and branched C6-C22 fatty alcoholcarbonates such as, for example, dicaprylyl carbonate (Cetiol® CC),Guerbet carbonates based on fatty alcohols containing 6 to 18,preferably 8 to 10, carbon atoms, esters of benzoic acid with linearand/or branched C6 to C22 alcohols (for example Finsolv® TN), linear orbranched, symmetrical or nonsymmetrical dialkyl ethers containing 6 to22 carbon atoms per alkyl group such as, for example, dicaprylyl ether(Cetiol® OE), ring opening products of epoxidized fatty acid esters withpolyols and hydrocarbons or mixtures thereof.

It is to be understood that anti-oxidants are able to inhibit or preventthe undesired changes in the compositions to be protected caused byoxygen effects and other oxidative processes. The effect of theanti-oxidants consists in most cases in them acting as free-radicalscavengers for the free radicals which arise during autoxidation.

In a preferred embodiment, the anti-oxidant is selected from the groupconsisting of

-   -   amino acids (for example glycine, alanine, arginine, serine,        threonine, histidine, tyrosine, tryptophan) and derivatives        thereof,    -   imidazoles (e.g. urocanic acid) and derivatives thereof,    -   peptides, such as D,L-carnosine, D-carnosine, L-carnosine        (=β-Alanyl-L-histidine) and derivatives thereof    -   carotenoids, carotenes (e.g. alpha-carotene, beta-carotene,        lycopene, lutein) or derivatives thereof,    -   chlorogenic acid and derivatives thereof,    -   lipoic acid and derivatives thereof (for example dihydrolipoic        acid),    -   auro-thioglucose, propylthiouracil and other thiols (for example        thioredoxin, glutathione, cysteine, cystine, cystamine and the        glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and        lauryl, palmitoyl, oleyl, gamma-linoleyl, cholesteryl and        glyceryl esters thereof) and salts thereof,    -   dilauryl thiodipropionate, distearyl thiodipropionate,        thiodipropionic acid and derivatives thereof (esters, ethers,        peptides, lipids, nucleotides, nucleosides and salts),    -   sulfoximine compounds (for example buthionine sulfoximines,        homocysteine sulfoximine, buthionine sulfones, penta-, hexa-,        heptathionine sulfoximine)    -   (metal) chelating agents (e.g. alpha-hydroxy fatty acids,        palmitic acid, phytic acid, lactoferrin),    -   alpha-hydroxy acids (for example citric acid, lactic acid, malic        acid),    -   humic acid, bile acid, bile extracts, bilirubin, biliverdin,        boldin (=alkaloid from the plant Peumus boldus, boldo extract,    -   EDTA, EGTA and derivatives thereof,    -   unsaturated fatty acids and derivatives thereof (e.g.        gamma-linolenic acid, linoleic acid, oleic acid),    -   folic acid and derivatives thereof,    -   ubiquinone and ubiquinol and derivatives thereof,    -   vitamin C and derivatives (for example ascorbyl palmitate, Mg        ascorbyl phosphate, ascorbyl acetate),    -   tocopherols and derivatives (for example vitamin E acetate),    -   vitamin A and derivatives (for example vitamin A palmitate),    -   coniferyl benzoate of gum benzoin, rutic acid and derivatives        thereof, alpha-glycosylrutin, ferulic acid,        furfurylideneglucitol,    -   butylhydroxytoluene (BHT), butylhydroxyanisole (BHA)    -   nordihydroguaiacic acid, nordihydroguaiaretic acid,        trihydroxybutyrophenone, uric acid and derivatives thereof,        mannose and derivatives thereof,    -   superoxide dismutase    -   zinc and derivatives thereof (for example ZnO, ZnSO4),    -   selenium and derivatives thereof (for example selenomethionine)        and    -   stilbenes and derivatives thereof (e.g. stilbene oxide,        trans-stilbene oxide)

In a preferred embodiment, the anti-oxidant is selected from the groupconsisting of pentaerythrityl, tetra-di-t-butyl-hydroxyhydrocinnamate,nordihydroguaiaretic acid, ferulic acid, resveratrol, propyl gallate,butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), ascorbyl palmitateand tocopherol.

In yet another preferred embodiment, the compositions according to thepresently claimed invention can comprise the anti-oxidant in an amountof 0.001 to 25 wt.-%, preferably 0.005 to 10 wt.-%, more preferably 0.01to 8 wt.-%, yet more preferably 0.025 to 7 wt.-%, even more preferably0.05 to 5 wt.-%, based on the total weight of the composition.

Deodorizing compositions (deodorants and antiperspirants) counteract,mask or eliminate body odors. Body odors are formed through the actionof skin bacteria on apocrine perspiration which results in the formationof unpleasant-smelling degradation products.

One embodiment of the invention is therefore directed to a compositioncomprising the compound of the present invention and at least onedeodorant-active agent. In a preferred embodiment, the deodorant-activeagent is selected from the groups consisting of anti-perspirants,esterase inhibitors and antibacterial agents.

Suitable antiperspirant is selected from the group consisting of saltsof aluminum, zirconium or zinc. Examples are aluminum chloride, aluminumchlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrateand complex compounds thereof, for example with 1,2-propylene glycol,aluminum hydroxyallantoinate, aluminum chloride tartrate, aluminumzirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate,aluminum zirconium pentachlorohydrate and complex compounds thereof, forexample with amino acids, such as glycine. Aluminum chlorohydrate,aluminum zirconium tetrachlorohydrate, aluminum zirconiumpentachlorohydrate and complex compounds thereof are preferably used.

In a preferred embodiment, the anti-perspirant is selected from thegroup consisting of aluminum chloride, aluminum chlorohydrate, aluminumdichlorohydrate, aluminum sesquichlorohydrate, aluminumhydroxyallantoinate, aluminum chloride tartrate, aluminum zirconiumtrichlorohydrate, aluminum zirconium tetrachlorohydrate and aluminumzirconium pentachlorohydrate.

Where perspiration is present in the underarm region, extracellularenzymes-esterases, mainly proteases and/or lipases are formed bybacteria and split the esters present in the perspiration, releasingodors in the process. Suitable esterase inhibitors are for exampletrialkyl citrates, such as trimethyl citrate, tripropyl citrate,triisopropyl citrate, tributyl citrate and, in particular, triethylcitrate. Esterase inhibitors inhibit enzyme activity and thus reduceodor formation. The free acid is probably released by the cleavage ofthe citric acid ester and reduces the pH value of the skin to such anextent that the enzymes are inactivated by acylation. Other esteraseinhibitors are sterol sulfates or phosphates such as, for example,lanosterol, cholesterol, campesterol, stigmasterol and sitosterolsulfate or phosphate, dicarboxylic acids and esters thereof, for exampleglutaric acid, glutaric acid monoethyl ester, glutaric acid diethylester, adipic acid, adipic acid monoethyl ester, adipic acid diethylester, malonic acid and malonic acid diethyl ester, hydroxycarboxylicacids and esters thereof, for example citric acid, malic acid, tartaricacid or tartaric acid diethyl ester, and zinc glycinate.

In a preferred embodiment, the esterase inhibitor is selected from thegroup consisting of trimethyl citrate, tripropyl citrate, triisopropylcitrate, tributyl citrate triethyl citrate, lanosterol, cholesterol,campesterol, stigmasterol, sitosterol sulfate, sitosterol phosphate,glutaric acid, glutaric acid monoethyl ester, glutaric acid diethylester, adipic acid, adipic acid monoethyl ester, adipic acid diethylester, malonic acid, malonic acid diethyl ester, citric acid, malicacid, tartaric acid, tartaric acid diethyl ester and zinc glycinate.

The compositions according to the presently claimed invention comprisesthe esterase inhibitor in the range of 0.01 to 20 wt.-%, preferably 0.1to 10 wt.-% and more particularly 0.5 to 5 wt.-%, based on the totalweight of the composition.

The term “anti-bacterial agents” as used herein encompasses substanceswhich have bactericidal and/or bacteriostatic properties. Typicallythese substances act against gram-positive bacteria such as, forexample, 4-hydroxybenzoic acid and salts and esters thereof,N-(4-chlorophenyl)-N′-(3,4-dichlorophenyl)-urea,2,4,4′-trichloro-2′-hydroxydiphenylether (triclosan),4-chloro-3,5-dimethylphenol,2,2′-methylene-bis-(6-bromo-4-chlorophenol),3-methyl-4-(1-methylethyl)-phenol, 2-benzyl-4-chlorophenol,3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propinyl butyl carbamate,chlorhexidine, 3,4,4′-trichlorocarbanilide (TTC), phenoxyethanol,glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate(GML), diglycerol monocaprate (DMC), salicylic acid-N-alkylamides suchas, for example, salicylic acid-n-octyl amide or salicylic acid-n-decylamide.

In a preferred embodiment, the antibacterial agent is selected from thegroup consisting of chitosan, phenoxyethanol,5-chloro-2-(2,4-dichlorophenoxy)-phenol, 4-hydroxybenzoic acid and saltsand esters thereof, N-(4-chlorophenyl)-N′-(3,4-dichlorophenyl)-urea,2,4,4′-trichloro-2′-hydroxydiphenylether (triclosan),4-chloro-3,5-dimethylphenol,2,2′-methylene-bis-(6-bromo-4-chlorophenol),3-methyl-4-(1-methylethyl)-phenol, 2-benzyl-4-chlorophenol,3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propinyl butyl carbamate,chlorhexidine, 3,4,4′-trichlorocarbanilide (TTC), phenoxyethanol,glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate(GML), diglycerol monocaprate (DMC), salicylic acid-N-alkylamides. Thecomposition according to the presently claimed invention comprises theantibacterial agent in the range of 0.01 to 5 wt. % and preferably 0.1to 2 wt.-%, based on the total weight of the composition.

In a preferred embodiment, the composition preferably comprises asurfactant. Due to the characteristic fragrance property of the compoundof the present invention and its substantivity, tenacity as well asstability, it can especially be used to provide an odor, preferably afragrance impression or aroma impression to surfactant-containingcompositions such as, for example, cleaners (in particular laundry careproducts and all-purpose cleaners). It can preferably be used to imparta long-lasting a flowery and/or a marine and/or a green and/or a sweetnote and/or a rubbery note and/or a nutty note and/or a woody noteand/or a dusty note and/or a rooty note and/or a lemon note odiferousimpression to a surfactant comprising composition.

In a preferred embodiment, the surfactant is selected from the groupconsisting of anionic, non-ionic, cationic, amphoteric and zwitterionicsurfactants. In yet another preferred embodiment, the surfactant is ananionic surfactant.

The compositions according to the presently claimed invention can thuspreferably comprise at least one surfactant. The surfactant(s) may beselected from anionic, non-ionic, cationic and/or amphoteric orzwitterionic surfactants. Surfactant-containing compositions, such asfor example shower gels, foam baths, shampoos, etc., preferably containat least one anionic surfactant.

The compositions according to the invention usually contain thesurfactant(s), in the aggregate, in an amount of 0 to 40 wt. %,preferably 0 to 20 wt. %, more preferably 0.1 to 15 wt. %, andparticularly 0.1 to 10 wt. %, based on the total weight of thecomposition. Typical examples of nonionic surfactants are fatty alcoholpolyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycolesters, fatty acid amide polyglycol ethers, fatty amine polyglycolethers, alkoxylated triglycerides, mixed ethers and mixed formals,optionally partly oxidized alk(en)yl oligoglycosides or glucuronic acidderivatives, fatty acid-N-alkyl glucamides, protein hydrolysates(particularly wheat-based vegetable products), polyol fatty acid esters,sugar esters, sorbitan esters, polysorbates and amine oxides. If thenonionic surfactants contain polyglycol ether chains, they may have aconventional homolog distribution, although they preferably have anarrow-range homolog distribution.

Zwitterionic surfactants are surface-active compounds which contain atleast one quaternary ammonium group and at least one COO(—) or SO3(-)group in the molecule. Particularly suitable zwitterionic surfactantsare the so-called betaines, such as the N-alkyl-N,N-dimethyl ammoniumglycinates, for example, cocoalkyl dimethyl ammonium glycinate,N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for example,cocoacylaminopropyl dimethyl ammonium glycinate, and2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazolines, containing 8 to 18carbon atoms in the alkyl or acyl group, and cocoacylaminoethylhydroxyethyl carboxymethyl glycinate. The fatty acid amide derivativeknown under the CTFA name of Cocamidopropyl Betaine is particularlypreferred.

Ampholytic surfactants are also suitable, particularly asco-surfactants. Ampholytic surfactants are surface-active compoundswhich, in addition to a C8 to C18 alkyl or acyl group, contain at leastone free amino group and at least one —COOH or —SO₃H group in themolecule and which are capable of forming inner salts. Examples ofsuitable ampholytic surfactants are N-alkyl glycines, N-alkyl propionicacids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids,N-hydroxyethyl-N-alkylamidopropyl glycines, N-alkyl taurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acidscontaining around 8 to 18 carbon atoms in the alkyl group. Particularlypreferred ampholytic surfactants are N-cocoalk-ylaminopropionate,cocoacylaminoethyl aminopropionate and acyl sarcosine.

Anionic surfactants are characterized by a water-solubilizing anionicgroup such as, for example, a carboxylate, sulfate, sulfonate orphosphate group and a lipophilic group. Dermatologically safe anionicsurfactants are known to the practitioner in large numbers from relevanttextbooks and are commercially available. They are, in particular, alkylsulfates in the form of their alkali metal, ammonium or alkanolammoniumsalts, alkylether sulfates, alkylether carboxylates, acyl isethionates,acyl sarcosinates, acyl taurines containing linear C12-C18 alkyl or acylgroups and sulfosuccinates and acyl glutamates in the form of theiralkali metal or ammonium salts.

Particularly suitable cationic surfactants are quaternary ammoniumcompounds, preferably ammonium halides, more especially chlorides andbromides, such as alkyl trimethyl ammonium chlorides, dialkyl dimethylammonium chlorides and trialkyl methyl ammonium chlorides, for example,cetyl trimethyl ammonium chloride, stearyl trim ethyl ammonium chloride,distearyl dimethyl ammonium chloride, lauryl dimethyl ammonium chloride,lauryl dimethyl benzyl ammonium chloride and tricetyl methyl ammoniumchloride. In addition, the readily biodegradable quaternary estercompounds, such as, for example, the dialkyl ammonium methosulfates andmethyl hydroxyalkyl dialkoyloxyalkyl ammonium methosulfates marketedunder the name of Stepantexe and the corresponding products of theDehyquarte series, may be used as cationic surfactants. “Esterquats” aregenerally understood to be quaternized fatty acid triethanolamine estersalts. They can provide the compositions with particular softness. Theyare known substances which are prepared by the relevant methods oforganic chemistry. Other cationic surfactants suitable for use inaccordance with the invention are the quaternized protein hydrolysates.

One embodiment of the presently claimed invention is directed to acomposition which is selected from the group consisting of perfumecompositions, body care compositions, hygiene articles, cleaningcompositions, textile detergent compositions, compositions for scentdispensers, foods, food supplements, pharmaceutical compositions andcrop protection compositions.

Said composition is preferably an aroma chemical composition, morepreferably a fragrance composition.

Suitable compositions are for example perfume compositions, body carecompositions (including cosmetic compositions and products for oral anddental hygiene), hygiene articles, cleaning compositions (includingdishwashing compositions), textile detergent compositions, compositionsfor scent dispensers, foods, food supplements, pharmaceuticalcompositions and crop protection compositions.

Perfume compositions can be selected from fine fragrances, airfresheners in liquid form, gel-like form or a form applied to a solidcarrier, aerosol sprays, scented cleaners, perfume candles and oils,such as lamp oils or oils for massage. Examples for fine fragrances areperfume extracts, Eau de Parfums, Eau de Toilettes, Eau de Colognes, Eaude Solide and Extrait Parfum.

Body care compositions include cosmetic compositions and products fororal and dental hygiene, and can be selected from after-shaves,pre-shave products, splash colognes, solid and liquid soaps, showergels, shampoos, shaving soaps, shaving foams, bath oils, cosmeticemulsions of the oil-in-water type, of the water-in-oil type and of thewater-in-oil-in-water type, such as e.g. skin creams and lotions, facecreams and lotions, sunscreen creams and lotions, after-sun creams andlotions, hand creams and lotions, foot creams and lotions, hair removalcreams and lotions, after-shave creams and lotions, tanning creams andlotions, hair care products such as e.g. hairsprays, hair gels, settinghair lotions, hair conditioners, hair shampoo, permanent andsemi-permanent hair colorants, hair shaping compositions such as coldwaves and hair smoothing compositions, hair tonics, hair creams and hairlotions, deodorants and antiperspirants such as e.g. underarm sprays,roll-ons, deodorant sticks and deodorant creams, products of decorativecosmetics such as e.g. eye-liners, eye-shadows, nail varnishes,make-ups, lipsticks and mascara, and products for oral and dentalhygiene, such as toothpaste, dental floss, mouth wash, breathfresheners, dental foam, dental gels and dental strips.

Hygiene articles can be selected from joss sticks, insecticides,repellents, propellants, rust removers, perfumed freshening wipes,armpit pads, baby diapers, sanitary towels, toilet paper, cosmeticwipes, pocket tissues, dishwasher and deodorizer.

Cleaning compositions, such as e.g. cleaners for solid surfaces, can beselected from perfumed acidic, alkaline and neutral cleaners, such ase.g. floor cleaners, window cleaners, dishwashing compositions both forhandwashing and machine washing use, bath and sanitary cleaners,scouring milk, solid and liquid toilet cleaners, powder and foam carpetcleaners, waxes and polishes such as furniture polishes, floor waxes,shoe creams, disinfectants, surface disinfectants and sanitary cleaners,brake cleaners, pipe cleaners, limescale removers, grill and ovencleaners, algae and moss removers, mold removers, facade cleaners.

Textile detergent compositions can be selected from liquid detergents,powder detergents, laundry pretreatments such as bleaches, soakingagents and stain removers, fabric softeners, washing soaps, washingtablets.

Food means a raw, cooked, or processed edible substance, ice, beverageor ingredient used or intended for use in whole or in part for humanconsumption, or chewing gum, gummies, jellies, and confectionaries.

A food supplement is a product intended for ingestion that contains adietary ingredient intended to add further nutritional value to thediet. A dietary ingredient may be one, or any combination, of thefollowing substances: a vitamin, a mineral, an herb or other botanical,an amino acid, a dietary substance for use by people to supplement thediet by increasing the total dietary intake, a concentrate, metabolite,constituent, or extract. Food supplements may be found in many formssuch as tablets, capsules, soft gels, gel caps, liquids, or powders.

Pharmaceutical compositions comprise compositions which are intended foruse in the diagnosis, cure, mitigation, treatment, or prevention ofdisease as well as articles (other than food) intended to affect thestructure or any function of the body of man or other animals.

Crop protection compositions comprise compositions which are intendedfor the managing of plant diseases, weeds and other pests (bothvertebrate and invertebrate) that damage agricultural crops andforestry.

In a preferred embodiment, the composition further comprises at leastone auxiliary agent selected from the group consisting of preservatives,abrasives, anti-acne agents, agents to combat skin aging, anti-celluliteagents, antidandruff agents, anti-inflammatory agents,irritation-preventing agents, irritation-alleviating agents,astringents, sweat-inhibiting agents, antiseptics, anti-statics,binders, buffers, carrier materials, chelating agents, cell stimulants,care agents, hair removal agents, emulsifiers, enzymes, essential oils,fibers, film formers, fixatives, foam formers, foam stabilizers,substances for preventing foaming, foam boosters, fungicides, gellingagents, gel-forming agents, hair care agents, hair shaping agents, hairsmoothing agents, moisture-donating agents, moisturizing substances,humectant substances, bleaching agents, strengthening agents, stainremoval agents, optical brighteners, impregnating agents, soilrepellents, friction-reducing agents, lubricants, moisturizing creams,ointments, opacifiers, plasticizers, covering agents, polish, shineagents, polymers, powders, proteins, refatting agents, exfoliatingagents, silicones, skin-calming agents, skin-cleansing agents, skin careagents, skin-healing agents, skin lightening agents, skin-protectiveagents, skin-softening agents, cooling agents, skin-cooling agents,warming agents, skin-warming agents, stabilizers, UV-absorbent agents,UV filters, fabric softeners, suspending agents, skin-tanning agents,thickeners, vitamins, waxes, fats, phospholipids, saturated fatty acids,mono- or polyunsaturated fatty acids, α-hydroxy acids, polyhydroxy fattyacids, liquefiers, dyes, color-protection agents, pigments,anti-corrosives, polyols, electrolytes and silicone derivatives.

For example, the method can be carried out by mixing the compound of thepresently claimed invention described herein and:

-   (i) at least one additional aroma chemical different from the    compound/mixture of the present invention, or-   (ii) at least one non-aroma chemical carrier, or-   (iii) both of (i) and (ii).

The invention is also directed to a method for modifying the aromacharacter (e.g., scent character) of an aroma chemical composition suchas, e.g., a fragranced composition, in particular a fragrancedready-to-use composition, wherein the method comprises incorporating thecompound of the presently claimed invention described herein into anaroma chemical composition such as, e.g., into a fragranced composition,in particular into a fragranced ready-to-use composition.

In particular, the invention is directed to a method of preparing aperfume composition, body care composition, hygiene article, cleaningcomposition, textile detergent composition, composition for scentdispensers, food, food supplement, pharmaceutical composition or cropprotection composition, comprising including the compound of thepresently claimed invention described herein in a perfume composition,body care composition, hygiene article, cleaning composition, textiledetergent composition, composition for scent dispensers, food, foodsupplement, pharmaceutical composition or crop protection composition.

In one embodiment the invention is directed to a method for imparting anote reminiscent of sweet, fruity, floral, orris, powdery elements to aperfume composition, body care composition, hygiene article, cleaningcomposition, textile detergent composition, composition for scentdispensers, food, food supplement, pharmaceutical composition or cropprotection composition, which comprises including a compound of thepresently claimed invention in a perfume composition, body carecomposition, hygiene article, cleaning composition, textile detergentcomposition, composition for scent dispensers, food, food supplement,pharmaceutical composition or crop protection composition.

Embodiments

In the following, there is provided a list of embodiments to furtherillustrate the present disclosure without intending to limit thedisclosure to the specific embodiments listed below.

-   -   1. Use of a compound selected from the group consisting of        dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol,        dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol,        11-dodecen-1-ol and dodecan-1-ol to impart an aroma impression        to a composition.    -   2. Use of a compound selected from the group consisting of        dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol,        dodeca-4,11-dien-1-ol, to impart an aroma impression to a        composition.    -   3. Method of imparting an aroma impression to a composition        comprising at least the step of adding a compound selected from        the group consisting of dodeca-4,8-dien-1-ol,        dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol,        8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol to a        composition.    -   4. Method of imparting an aroma impression to a composition        comprising at least the step of adding a compound selected from        the group consisting of dodeca-4,8-dien-1-ol,        dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, to a composition.    -   5. The use or method according to embodiments 1 to 4, wherein        the compounds are selected from (4Z,8E)-dodeca-4,8-dien-1-ol,        (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol,        (4Z,8Z)-dodeca-4,8-dien-1-ol, (8E)-dodeca-4,8-dien-1-ol,        (8Z)-dodeca-4,8-dien-1-ol, (4E)dodeca-4,11-dien-1-ol,        (4Z)dodeca-4,11-dien-1-ol.    -   6. The use or method according to any of the preceding        embodiments, wherein the composition is selected from perfume        compositions, body care compositions, hygiene articles, cleaning        compositions, textile detergent compositions, compositions for        scent dispensers, foods, food supplements, pharmaceutical        compositions and crop protection compositions.    -   7. The use or method according to any of the preceding        embodiments, wherein the impression is selected from the group        consisting of an aldehydic note, a fatty note, a mandarin note,        a clean linen note, a floral note, a marine note, a citrus note,        a metallic note, a waxy note and a green note.    -   8. The use or method according to any of the preceding        embodiments, wherein the compound is present in an amount in the        range of ≥0.01 wt. % to ≤70.0 wt. %, based on the total weight        of the composition.    -   9. A mixture comprising,        -   a) at least one compound selected from the group consisting            of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol and            dodeca-4,11-dien-1-ol; and        -   b) at least one compound selected from the group consisting            of 4-dodecen-1-ol, 8-dodecen-1-ol and 11-dodecen-1-ol.    -   10. The mixture according to embodiment 9, wherein        dodeca-4,8-dien-1-ol is selected from        (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol,        (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol, and        mixtures of two or more thereof.    -   11. The mixture according to embodiment 9, wherein        dodeca-8,11-dien-1-ol is selected from (8E)-dodeca-4,8-dien-1-ol        and (8Z)-dodeca-4,8-dien-1-ol.    -   12. The mixture according to embodiment 9, wherein        dodeca-4,11-dien-1-ol is selected from        (4E)-dodeca-4,11-dien-1-ol and (4Z)-dodeca-4,11-dien-1-ol.    -   13. The mixture according to embodiment 9, wherein        4-dodecen-1-ol is selected from (4E)-dodecen-1-ol and        (4Z)-dodecen-1-ol.    -   14. The mixture according to embodiment 9, wherein        8-dodecen-1-ol is selected from (8E)-dodecen-1-ol and        (8Z)-dodecen-1-ol.    -   15. The mixture according to any of the embodiments 9 to 14,        wherein the mixture comprises        -   a) any one or more compound selected from (4E)-dodecen-1-ol,            (4Z)-dodecen-1-ol, (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol,            or        -   b) any one or more compound selected from            (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol,            (4E,8E)-dodeca-4,8-dien-1-ol and            (4Z,8Z)-dodeca-4,8-dien-1-ol, or        -   c) any one or more compound selected from (a) and (b).    -   16. The mixture according to any of the embodiments 9 to 14,        wherein the mixture further comprises dodecan-1-ol.    -   17. Use of the mixture according to any one of embodiments 9 to        16 as an aroma chemical.    -   18. Use of the mixture according to any one of embodiments 9 to        16 for preparing an aroma chemical composition.    -   19. Use of the mixture according to any one of embodiments 9 to        16 for modifying the aroma character of an aroma chemical        composition.    -   20. Aroma chemical composition according to embodiments 1 to 8        or the mixture according to embodiments 15 to 16 comprising:        -   (i) at least one additional aroma chemical        -   (ii) at least one non-aroma chemical carrier, or        -   (iii) a mixture of (i) and (ii).    -   21. The aroma chemical composition of embodiment 20, which is an        aromatized ready-to-use composition.    -   22. The aroma chemical composition of embodiment 21, wherein the        aromatized ready-to-use composition is selected from the group        consisting of perfume compositions, body care compositions,        hygiene articles, cleaning compositions, textile detergent        compositions, compositions for scent dispensers, foods, food        supplements, pharmaceutical compositions and crop protection        compositions.    -   23. A method of preparing the compound as defined in any of        embodiments 1 to 5, wherein the method comprises at least the        steps of:        -   (i) subjecting dodeca-4,8,11-trienal to a reduction reaction            and hydrogenation and, optionally        -   (ii) isolating the compounds.

Preferred Embodiments

-   -   1. A mixture comprising,        -   a) at least one compound selected from the group consisting            of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol and            dodeca-4,11-dien-1-ol; and        -   b) at least one compound selected from the group consisting            of 4-dodecen-1-ol, 8-dodecen-1-ol and 11-dodecen-1-ol.    -   2. The mixture according to embodiment 1, wherein        dodeca-4,8-dien-1-ol is selected from        (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol,        (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol, and        mixtures of two or more thereof.    -   3. The mixture according to embodiment 1, wherein        dodeca-8,11-dien-1-ol is selected from (8E)-dodeca-4,8-dien-1-ol        and (8Z)-dodeca-4,8-dien-1-ol.    -   4. The mixture according to embodiment 1, wherein        dodeca-4,11-dien-1-ol is selected from        (4E)-dodeca-4,11-dien-1-ol and (4Z)-dodeca-4,11-dien-1-ol.    -   5. The mixture according to embodiment 1, wherein 4-dodecen-1-ol        is selected from (4E)-dodecen-1-ol and (4Z)-dodecen-1-ol.    -   6. The mixture according to embodiment 1, wherein 8-dodecen-1-ol        is selected from (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol.    -   7. The mixture according to any of the embodiments 1 to 6,        wherein the mixture comprises a) any one or more compound        selected from (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol,        (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol, or        -   b) any one or more compound selected from            (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol,            (4E,8E)-dodeca-4,8-dien-1-ol and            (4Z,8Z)-dodeca-4,8-dien-1-ol, or        -   c) any one or more compound selected from (a) and (b).    -   8. The mixture according to any of the embodiments 1 to 7,        wherein the mixture further comprises dodecan-1-ol.    -   9. Use of the mixture according to any one of embodiments 1 to 8        as an aroma chemical.    -   10. Use of the mixture according to any one of embodiments 1 to        8 for preparing an aroma chemical composition.    -   11. Use of the mixture according to any one of embodiments 1 to        8, for modifying the aroma character of an aroma chemical        composition    -   12. Aroma chemical composition comprising the mixture according        to embodiments 1 to 8 and        -   (i) at least one additional aroma chemical        -   (ii) at least one non-aroma chemical carrier, or        -   (iii) a mixture of (i) and (ii).    -   13. The aroma chemical composition of embodiment 12, which is an        aromatized ready-to-use composition.    -   14. The aroma chemical composition of embodiment 13, wherein the        aromatized ready-to-use composition is selected from the group        consisting of perfume compositions, body care compositions,        hygiene articles, cleaning compositions, textile detergent        compositions, compositions for scent dispensers, foods, food        supplements, pharmaceutical compositions and crop protection        compositions.    -   15. Use of a compound selected from the group consisting of        dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol,        dodeca-4,11-dien-1-ol to impart an aroma impression to a        composition.    -   16. Method of imparting an aroma impression to a composition        comprising at least the step of adding a compound selected from        the group consisting of dodeca-4,8-dien-1-ol,        dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol to a composition.    -   17. The use or method according to embodiment 15 or 16, wherein        the compounds are selected from (4Z,8E)-dodeca-4,8-dien-1-ol,        (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol,        (4Z,8Z)-dodeca-4,8-dien-1-ol, (8E)-dodeca-4,8-dien-1-ol,        (8Z)-dodeca-4,8-dien-1-ol, (4E)dodeca-4,11-dien-1-ol,        (4Z)dodeca-4,11-dien-1-ol.    -   18. The use or method according to any of the embodiments 15 to        17, wherein the composition is selected from perfume        compositions, body care compositions, hygiene articles, cleaning        compositions, textile detergent compositions, compositions for        scent dispensers, foods, food supplements, pharmaceutical        compositions and crop protection compositions.    -   19. The use or method according to any of the embodiments 15 to        17, wherein the impression is selected from the group consisting        of an aldehydic note, a fatty note, a mandarin note, a clean        linen note, a floral note, a marine note, a citrus note, a        metallic note, a waxy note and a green note.    -   20. The use or method according to any of the embodiments 15 to        17, wherein the compound is present in an amount in the range of        ≥0.01 wt. % to ≤70.0 wt. %, based on the total weight of the        composition

EXAMPLES

The present invention is illustrated in detail by non-restrictiveworking examples which follow. More particularly, the test methodsspecified hereinafter are part of the general disclosure of theapplication and are not restricted to the specific working examples.

Analytical Method:

The characterization is done by ¹³C-NMR. The ¹³C-NMR spectra weremeasured on a Bruker DPX-500 spectrometer

GC method: Stabilwax 60m GC-column coupled with a TOF Mass-SpectrometryFI (Field Ionization).

-   1. Preparation of the mixture of 4,8-Dodecadien-1-ol as well as    4-Dodecadien-1-ol and 8-Dodecadien-1-ol as mixture of cis/trans    isomers.

4,8,11-Dodecatrienal (1,2 Kg, 82 mmol) was dissolved in methanol (800 g)in 3,5 L autoclave in the presence of trimethylamine (48 g, 3 wt. %) andRu/Fe-based catalyst (20 g, 1.6 wt. %). The hydrogenation reaction wasperformed at T=55° C. and 30 bar of hydrogen pressure yielding4,8-Dodecadien-1-ol as well as 4-Dodecadien-1-ol and 8-Dodecadien-1-olas mixture of cis/trans isomers.

1H NMR: mixture of products: (500 MHz; CDCl3): δ [ppm]=5,42-5,32 (m),3,61-3,57 (m), 2,1-1,9 (m), 1,62-1,56 (m), 1,35-1,23 (m).

Depending on hydrogenation time different ratio of the correspondingalcohols determined by H-NMR (olefin vs methylene).

Experiment Ratio dodecenol/dodecadienol Reaction Time 1a 12%/88%  6 hrs1b 40%/60%  8 hrs 1c 66%/34% 14 hrs

-   2. Olfactory assessment

In order to test the quality and intensity of the odor ofdodeca-4,8-dien-1-ol, dodeca-8,11-dien-d-ol, dodeca-4,11-dien-1-ol,4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol, dodecan-1-ol scentstrip tests were performed.

For this purpose, strips of absorbent paper were dipped into a solutioncontaining 1 to 10 wt. % of the compound to be tested in ethanol. Afterevaporation of the solvent (about 30 s) the scent impression wasolfactively evaluated by a trained perfumer.

Results:

TABLE 1 Results of the scent tests Example no. Compound/Isomer mixtureOdor Description 1 (4E)-dodecen-1-ol, (4Z)- aldehydic, fatty,dodecen-1-ol, (8E)-dodecen- mandarin, clean 1-ol, (8Z)-dodecen-1-ol,linen, floral note, a (4Z,8E)-dodeca-4,8-dien-1-ol, marine note, acitrus (4E,8Z)-dodeca-4,8-dien-1-ol, note, metallic note,(4E,8E)-dodeca-4,8-dien-1-ol, waxy note and a(4Z,8Z)-dodeca-4,8-dien-1-ol, green note dodecan-1-ol

Advantageous Perfume Components

The compound of example 1 was formulated in the perfume compositionsaccording to tables 2 and 3 and was labelled as compound A.

TABLE 2 Fragrance compositions 1A and 1B 1A 1B Lactone C10 gamma(5-hexyloxolan-2-one) 2 2 Bourgeonal (3-(4-tert-butylphenyl)propanal) 22 Citronellol 3 3 Aldehyde C-14 (5-heptyloxolan-2-one) 3 3 Allylheptylate 4 4 Amber core (1-(2-tert-butylcyclohexyl)oxybutan-2-ol) 4 4Ethyl-2-methyl butyrate 4 4 Geranyl acetate 5 5 Helional(3-(1,3-benzodioxol-5-yl)-2-methylpropanal) 10 10 Manzanate (ethyl2-methylpentanoate) 10 10 Amberwood (ethoxymethoxycyclododecane) 10 10Hexyl acetate 11 11 Benzyl salicylate 12 12 Magnolan(2,4-dimethyl-4,4a,5,9b-tetrahydroindeno 15 15 [1,2-d][1,3]dioxine)Verdox (2-tert-butylcyclohexyl)acetate) 25 25 Bergamot oil bergaptenefree 25 25 Linalol 30 30 Dipropylene glycol 45 45 Iso E Super(Tetramethyl acetyloctahydronaphthalenes) 110 110 Pyranol(4-methyl-2-(2-methylpropyl)oxan-4-ol) 170 170 Hedione (methyl3-oxo-2-pentylcyclopentaneacetate) 200 200 Galaxolide 50% IPM(1,3,4,6,7,8-hexahydro-4,6,6,7, 300 3008,8-hexamethylcyclopenta(g)-2-benzopyran 50% in isopropyl myristate)Compound A 5 20 1005 1020

TABLE 3 Fragrance compositions 2A and 2B 2A 2B Raspberry ketone(4-(4-hydroxyphenyl)butan-2-one) 4 4 Vanitrope(2-ethoxy-5-prop-1-enylphenol) 6 6 Cyclamen aldehyde (at least 90%2-methyl-3-(p- 10 10 isopropylphenyl)propionaldehyde; secondarycomponent: 5% 3-(p-cumenyl)-2-methylpropionic acid) Bicyclononalactone(3,4,4a,5,6,7,8,8a- 10 10 octahydrochromen-2-one) Aldehyde C-14(5-heptyloxolan-2-one) 14 14 Ethylvanillin(3-ethoxy-4-hydroxybenzaldehyde) 16 16 Heliotropine(1,3-benzodioxole-5-carbaldehyde) 20 20 Iso E Super (tetramethylacetyloctahydronaphthalenes) 20 20 Sandela(3-[5,5,6-trimethylbicyclo[2.2.1]hept-2- 30 30 yl]cyclohexan-1-ol)Vanillin isobutyrate ((4-formyl-2-methoxyphenyl)2- 40 40methylpropanoate) Aldehyde C-18 (5-pentyloxolan-2-one) 50 50 Benzylsalicylate 60 60 Hexyl cinnamic aldehyde (2-(phenylmethylidene) 70 70octanal) Hedione (methyl 3-oxo-2-pentylcyclopentaneacetate) 130 130Pyranol (4-methyl-2-(2-methylpropyl)oxan-4-ol) 150 150 Ethylenebrassylate (1,4-dioxacycloheptadecane-5,17- 170 170 dione) Galaxolide50% IPM (1,3,4,6,7,8-hexahydro-4,6,6,7, 200 2008,8-hexamethylcyclopenta(g)-2-benzopyran 50% in isopropyl myristate)Compound A 5 20 1005 1020

The example 1 or example 2 in table 1, fragrance composition accordingto table 2, table 3 namely 1A, 1B, 2A, 2B could be included in variouscompositions enlisted below;

-   -   Deo pump spray    -   Clean hair conditioner    -   Face wash gel    -   Foam bath concentrate    -   Hair gel    -   Self foaming bodywash    -   Sprayable sun care emulsion    -   Sprayable sun protection emulsion    -   Emollient facial gel    -   2-phases oil foam bath    -   Shampoos    -   Shower bath    -   Hydro-alcoholic AP/Deo pump spray    -   Aerosol    -   Aqueous/alcoholic AP/Deo roll-on    -   Styling Gel Type “Out of Bed”    -   Shaving Foam    -   Sensitive skin Baby shampoo    -   Body wash for Sensitive Skin    -   Gloss Enhancing Shampoo for Sensitive Scalp    -   Deo Stick    -   Baby Wipe    -   After shave balm    -   Face Gel    -   Face Day Care Cream    -   Face Cleanser    -   Body lotion    -   Sun Care SPF50+, Sprayable Lotion    -   Hand dish cleaner, regular    -   Hand dish cleaner, concentrate    -   Sanitary cleaner, concentrate    -   All-purpose cleaner    -   Anti-bacterial fabric softener    -   Detergent composition    -   Powder detergent composition    -   Liquid detergent composition

A person skilled in art may be well versed with the various generalformulations for the above-mentioned products.

Perfume oil compositions 1A, 1B, 2A and 2B can for example be formulatedin specific formulations as disclosed in, IP.com Number: IPCOM000258614Dentitled New Aroma Chemicals pages 6 to 46, Table 1 to Table D13,wherein the “Fragrance Composition 1A” is replaced by identical amountsof perfume oil compositions 1A, 1B. 2A or 2B.

1.-21. (canceled)
 22. Use of a compound selected from the groupconsisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol,dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-oland dodecan-1-ol to impart an aroma impression to a composition. 23.Method of imparting an aroma impression to a composition comprising atleast the step of adding a compound selected from the group consistingof dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol,4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol to acomposition.
 24. The method according to claim 23, wherein the compoundsare selected from (4Z,8E)-dodeca-4,8-dien-1-ol,(4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol,(4Z,8Z)-dodeca-4,8-dien-1-ol, (8E)-dodeca-4,8-dien-1-ol,(8Z)-dodeca-4,8-dien-1-ol, (4E)dodeca-4,11-dien-1-ol,(4Z)dodeca-4,11-dien-1-ol, (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol,(8E)-dodecen-1-ol, (8Z)-dodecen-1-ol and dodecan-1-ol.
 25. The methodaccording to claim 23, wherein the composition is selected from perfumecompositions, body care compositions, hygiene articles, cleaningcompositions, textile detergent compositions, compositions for scentdispensers, foods, food supplements, pharmaceutical compositions andcrop protection compositions.
 26. The method according to claim 23,wherein the impression is selected from the group consisting of analdehydic note, a fatty note, a mandarin note, a clean linen note, afloral note, a marine note, a citrus note, a metallic note, a waxy noteand a green note.
 27. The method according to claim 23, wherein thecompound is present in an amount in the range of ≥0.01 wt. % to ≤70.0wt. %, based on the total weight of the composition.
 28. A mixturecomprising, a) at least one compound selected from the group consistingof dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol anddodeca-4,11-dien-1-ol; and b) at least one compound selected from thegroup consisting of 4-dodecen-1-ol, 8-dodecen-1-ol and 11-dodecen-1-ol.29. The mixture according to claim 28, wherein dodeca-4,8-dien-1-ol isselected from (4Z,8E)-dodeca-4,8-dien-1-ol,(4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol,(4Z,8Z)-dodeca-4,8-dien-1-ol, and mixtures of two or more thereof. 30.The mixture according to claim 28, wherein dodeca-8,11-dien-1-ol isselected from (8E)-dodeca-4,8-dien-1-ol and (8Z)-dodeca-4,8-dien-1-ol.31. The mixture according to claim 28 wherein dodeca-4,11-dien-1-ol isselected from (4E)-dodeca-4,11-dien-1-ol and (4Z)-dodeca-4,11-dien-1-ol.32. The mixture according to claim 28, wherein 4-dodecen-1-ol isselected from (4E)-dodecen-1-ol and (4Z)-dodecen-1-ol.
 33. The mixtureaccording to claim 28, wherein 8-dodecen-1-ol is selected from(8E)-dodecen-1-ol and (8Z)-dodecen-1-ol.
 34. The mixture according toclaim 28, wherein the mixture comprises a) any one or more compoundselected from (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol, (8E)-dodecen-1-oland (8Z)-dodecen-1-ol, or b) any one or more compound selected from(4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol,(4E,8E)-dodeca-4,8-dien-1-ol and (4Z,8Z)-dodeca-4,8-dien-1-ol, or c) anyone or more compound selected from (a) and (b).
 35. The mixtureaccording to claim 28, wherein the mixture further comprisesdodecan-1-ol.
 36. An aroma chemical composition comprising the mixtureaccording to claim
 28. 37. Use of the mixture according to claim 28 forpreparing an aroma chemical composition.
 38. A method for modifying thearoma character of an aroma chemical composition comprising adding themixture according to claim 28 to the aroma chemical composition. 39.Aroma chemical composition according to claim 36 comprising: (i) atleast one additional aroma chemical (ii) at least one non-aroma chemicalcarrier, or (iii) a mixture of (i) and (ii).
 40. The aroma chemicalcomposition of claim 39, which is an aromatized ready-to-usecomposition.
 41. The aroma chemical composition of claim 40, wherein thearomatized ready-to-use composition is selected from the groupconsisting of perfume compositions, body care compositions, hygienearticles, cleaning compositions, textile detergent compositions,compositions for scent dispensers, foods, food supplements,pharmaceutical compositions and crop protection compositions.
 42. Amethod of preparing a compound selected from the group consisting ofdodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol,4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol,wherein the method comprises at least the steps of: (i) subjectingdodeca-4,8,11-trienal to a reduction reaction and hydrogenation and,optionally (ii) isolating the compounds.